Acetic Acid → 3-Bromo-1-(2-chlorophenyl)propane-1,2-dione

HRID 216837Notes

Reaction equation

HRID 216837 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:12])[C:9](=[O:11])[CH3:10].[Br:13]Br.C(O)(=O)C.C(Cl)(Cl)Cl>>[Br:13][CH2:10][C:9](=[O:11])[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[O:12]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 24408BromineHCID 178656181-(2-Chlorophenyl)propane-1,2-dione

Product 1

HCID 575561703-Bromo-1-(2-chlorophenyl)propane-1,2-dione

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(2-chlorophenyl)propane-1,2-dione (4.2379 g, 23.208 mmol), bromine (1.1891 mL, 23.208 mmol), and glacial acetic acid (0.67005 mL, 11.604 mmol) in chloroform (58.020 mL, 23.208 mmol) was heated at 60° C. After 17 h of stirring at 60° C., the mixture was removed from heat and concentrated under reduced pressure to give 3-bromo-1-(2-chlorophenyl)propane-1,2-dione as an orange liquid: LC-MS: a peak of m/z 261.0 [M+H(79Br)]+ and 262.9 [M+H (81Br)-]+. The orange liquid was carried on crude without purification for the next step.

Workup

  1. customthe mixture was removed
  2. temperaturefrom heat
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-18db080b07d846f38acdb4af0608298f
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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